Process for preparing a 2(ω-aminoalkyl)-1,3-heterocyclic compounds

Abstract

2-(ω-AMINOALKYL)-1,3-HETEROCYCLIC COMPOUNDS ARE PREPARED BY REACTING A COMPOUND SELECTED FROM THE GROUP OF A DIAMINE, AN AMINOHYDROXY AND AN AMINOTHIOL COMPOUND, SAID COMPOUND HAVING THE FORMULA: ##EQU1## wherein ##EQU2## A is a bivalent chain of 2 or 3 carbon atoms, which can also be part of a bivalent, optionally substituted aliphatic, cycloaliphatic, araliphatic or aromatic radical, and X is oxygen, sulphur or the group ##EQU3## wherein R 7 is as defined herein with a lactam having the formula ##EQU4## WHEREIN B is selected from the group of a single bond, oxygen, sulphur, the group ##EQU5## wherein R 6 is as defined herein, and arylene, R 1 , r 2 , r 3 and R 4 , which may be the same or different, are selected from the group of hydrogen, halogen, nitro and optionally substituted aliphatic, cycloaliphatic, araliphatic and aromatic, R 5 , r 6 and R 7 , which may be the same or different, are selected from the group of hydrogen and optionally substituted aliphatic, cycloaliphatic, araliphatic and aromatic, and n and m, which may be the same or different, are intergers of from 1 to 14, with the proviso that the sum of n and m does not exceed 15, At a temperature of from 100° to 300°C in the presence of at least a catalytic quantity of an acid and/or an acid catalyst.

What is claimed is: 
     
       1. Process for preparing a 5-membered heterocycle which comprises reacting a diamine, aminohydroxy or aminothiol compound having the formula ##EQU13##wherein A is a bivalent aromatic radical selected from the group of o-phenylene and o-naphthylene and the foregoing substituted by halogen, nitro, amino which may also be mono- or di-substituted by lower alkyl, hydroxy, C 1-4  alkoxy, C 6-10  aryloxy, C 1-4  alkylmercapto, C 6-10  arylmercapto C 1-4  alkylsulfonyl or C 6-10  arylsulfonyl; X is oxygen, sulfur or the group   >N -- R.sup.7     wherein     R 7  is as defined herein with a lactam having the formula ##EQU14## wherein B is selected from the group of a single bond C 6-10  arylene, oxygen, sulfur and the group ##EQU15##wherein R 6  is as defined herein;   R 1 , r 2 , r 3  and R 4 , which may be the same or different, are selected from the group of hydrogen, halogen nitro, and alkyl having up to 18 carbon atoms, cycloalkyl having 4 to 12 carbon atoms, phenylalkyl having up to 5 carbon atoms in the alkyl portion, phenyl and naphthyl and the foregoing substituted by halogen, nitro, amino which may also be mono- or di- substituted by lower alkyl, hydroxy, C 1-4  alkoxy, C 6-10  aryloxy, C 1-4  alkylmercapto, C 6-10  arylmercapto, C 1-4  alkylsulfonyl or C 6-10  arylsulfonyl;   R 5 , r 6  and R 7 , which may be the same or different, are selected from the group of hydrogen and alkyl having up to 18 carbon atoms, cycloalkyl having 4 to 12 carbon atoms, phenylalkyl having up to 5 carbon atoms in the alkyl portion, phenyl and naphthyl and the foregoing substituted by halogen, nitro, amino which may also be mono- or di- substituted by lower alkyl, hydroxy, C 1-4  alkoxy, C 6-10  aryloxy, C 1-4  alkylmercapto, C 6-10  arylmercapto, C 1-4  alkylsulfonyl or C 6-10  arylsulfonyl; and   n and m which may be the same or different, are integers of from 1 to 14, with the proviso that the sum of n and m does not exceed 15, at a temperature of from 100° to 300°C in the presence of an acid selected from the group of mineral acids, aliphatic and aromatic sulfonic acids, aliphatic and aromatic phosphonic acids and Lewis acids and/or an acid catalyst selected from the group of acid activated silicas and fuller earths, natural and synthetic acid ion exchangers and acid activated molecular sieves, in an amount of from 0.0001 to 2 times the equivalent quantity per mole of the lactam.     
     
     
       2. Process for preparing a 5-membered heterocycle in claim 1 having the formula ##SPC6## wherein   X is oxygen, sulfur or the group   >N -- R.sup.7,       r 5  and R 7 , which may be the same or different, are selected from the group of hydrogen and alkyl having up to 18 carbon atoms, cycloalkyl having 4 to 12 carbon atoms, phenylalkyl having up to 5 carbon atoms in the alkyl portion, phenyl and naphthyl and the foregoing substituted by halogen, nitro, amino which may also be mono- or di- substituted by lower alkyl, hydroxy, C 1-4  alkoxy, C 6-10  aryloxy, C 1-4  alkylmercapto, C 6-10  arylmercapto C 1-4  alkylsulfonyl or C 6-10  arylsulfonyl,   R 8  and R 9  which may be the same or different are selected from the group of hydrogen, halogen, nitro, amino, which may also be mono or di- substituted by lower alkyl, hydroxy, C 1-4  alkoxy, C 6-10  aryloxy, C 1-4  alkylmercapto, C 6-10  arylmercapto, C 1-4  alkylsulfonyl and C 6-10  arylsulfonyl;   (n+m) represents a number from 2 to 15, wherein compounds having the formula: ##SPC7##   are reacted with compounds having the formula: ##EQU16##wherein X, R 5 , R 8 , R 9  and (n+m) are as defined above.     
     
     
       3. Process for preparing 2-(5'-aminopentyl)-substituted 1,3-heterocycles as in claim 1 wherein the lactam is ε-captolactam. 
     
     
       4. Process of claim 1 wherein linear or cyclic oligomers or polymers of the lactams are used. 
     
     
       5. Process of claim 1 wherein the reaction is carried out at a temperature of from 180°C to 250°C 
     
     
       6. Process of claim 1 wherein the amino compound is used in excess of between 0.2 and 3 times the minimum quantity which is required. 
     
     
       7. Process of claim 1 wherein water eliminated during the reaction is removed from the reaction mixture by distillation.